New prenyl flavanone and diarylbutanol from Uvaria siamensis stem bark and their α-glucosidase inhibitory activity

Nat Prod Res. 2024 Nov;38(22):3982-3988. doi: 10.1080/14786419.2023.2272024. Epub 2023 Oct 22.

Abstract

One new prenyl flavanone (1), (2S)-8-prenyl-5,6-dihydroxy-7-methoxyflavanone, and one new diarylbutanol (2), (7'S)-3'-hydroxy-linderagatin-A, were isolated from the stem bark of Uvaria siamensis (Annonaceae), along with five known compounds, eriodictyol (3), quercetin (4), paprazine (5), N-trans-caffeoyltyramine (6), and N-trans-feruloyltyramine (7). Their structures were determined through extensive spectroscopic analyses and comparison with the literature. The α-glucosidase inhibitory potential of 1-7 was evaluated. Compound 6 showed the highest inhibitory activity against α-glucosidase and exhibited superior potency compared to the positive control, with an IC50 value of 0.12 μM.

Keywords: (2S)-8-prenyl-5,6-dihydroxy-7-methoxyflavanone; (7’S)-3′-hydroxylinderagatin-A; Annonaceae; Uvaria siamensis; α-glucosidase inhibition.

MeSH terms

  • Butanols / chemistry
  • Coumaric Acids
  • Flavanones* / chemistry
  • Flavanones* / pharmacology
  • Glycoside Hydrolase Inhibitors* / chemistry
  • Glycoside Hydrolase Inhibitors* / pharmacology
  • Molecular Structure
  • Plant Bark* / chemistry
  • Plant Stems / chemistry
  • Quercetin / analogs & derivatives
  • Quercetin / chemistry
  • Quercetin / pharmacology
  • Tyramine / analogs & derivatives
  • Uvaria* / chemistry
  • alpha-Glucosidases* / metabolism

Substances

  • Glycoside Hydrolase Inhibitors
  • Flavanones
  • alpha-Glucosidases
  • eriodictyol
  • Butanols
  • feruloyltyramine
  • Quercetin
  • Coumaric Acids
  • Tyramine